JP2003113194A - New gold-sulfur compound and method for synthesizing the compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a new gold-sulfur compound useful as an intermediate for synthesizing pharmaceuticals, agricultural chemicals, and photographic materials. SOLUTION: This new gold (I)-sulfur compound is expressed by the general formula (1) [Ch is O or S; any one of R<1> and R<2> is a group expressed by the general formula (2) and the other is H or an alkyl; R<3> to R<10> are each H, an alkyl, hydroxy, amino, carboxy, an alkoxy, an aryloxy, an acyloxy, an acylamino or the like, provided that a compound expressed by the general formula (1) never comprises a thioglucose-gold (I) salt; L<1> in the general formula (2) is an amine, a nitrogen-containing heterocyclic compound, a thiol, a thioether, a disulfide, a thioamide, a selenoether, a diselenide, a selenoamide, a telluroether, a ditelluride, a telluroamide or the like; and n<1> is 0 or 1] or comprises its enantiomer.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to novel gold-chalcogen compounds useful as pharmaceuticals, agricultural chemicals, synthetic intermediates for photographic materials, and photographic additives, in particular silver halide photographic light-sensitive materials. It relates to a gold (I) -sulfur compound capable of improving the sensitivity.

[0002]

2. Description of the Related Art Gold-chalcogen compounds have high activity against living organisms and have been used as medicines for a long time. Also, gold-chalcogen compounds are often used in the field of silver halide photographic light-sensitive materials. Thus, gold-chalcogen compounds are very useful chemical species as synthetic intermediates and final products for these applications. Many gold-chalcogen compounds having a gold-sulfur bond are known. Among compounds having a bond between gold (I) and an anionic sulfide, a sulfur atom is substituted at the 1-position such as glucose. The compound of saccharides and gold is slightly
Only the mercaptoglucoside gold (I) salt described in 29274 is known. Also, J. Med. Che
m. 1972, 15, pages 1095 and J. Med. Chem. 1986, 29, 218.
, J. Med. Chem. 1987, 30, 2181 and the like, sugars such as glucose and mannose in which the sulfur atom is substituted at the 1-position, gold (I), alkylphosphine ligands and There are many known complexes with arylphosphine ligands. It has been found that the addition of this compound to a silver halide photographic light-sensitive material changes photographic performance (especially increases sensitivity during high-illuminance exposure).
At the same time, it was a problem to cause a large desensitization. Therefore, it has been desired to develop a compound having a higher effect of improving photographic properties and having no problem of desensitization.

[0003]

Therefore, a first object of the present invention is to provide a novel gold-chalcogen compound useful as a synthetic intermediate and a final product for pharmaceuticals, agricultural chemicals and photographic materials. . The second object is to provide a gold-chalcogen compound which has effective performance and does not cause desensitization when added to a photographic light-sensitive material.

[0004]

The objects of the present invention have been achieved by the following means. [1] A gold (I) -sulfur compound represented by the following general formula (1) or an enantiomer thereof. General formula (1)

[0005]

[Chemical 3]

[In the formula (1), Ch is an O atom or S
Represents an atom. One of R ¹ and R ² represents a group represented by the general formula (2), and the other represents a hydrogen atom or an alkyl group.
R ³ to R ^{1 0} are each a hydrogen atom, an alkyl group, hydroxy group,
An amino group, a carboxy group, an alkoxy group, an aryloxy group, an acyloxy group, an acylamino group, a sulfonamide group, an alkoxycarbonyl group, an aryloxycarbonyl group, or a carbamoyl group is represented, and the compound represented by the formula (1) is thio. It does not contain glucose gold (I) salts. ] General formula (2)

[0007]

[Chemical 4]

[In the formula (2), L¹Is replaced or nothing
Substituted amines, 5- to 6-membered nitrogen-containing heterocycles,
Thiols (and their proton dissociation products), Thioethe
, Disulfides, thioamides, selenoethers
, Diselenides, selenoamides, telluroethers
, Ditellurides, telluroamides, or P (R¹¹)
(R¹²) R ¹³(R¹¹~ R¹³Is a heterocyclic group, OR¹⁴, SR¹⁵, N (R¹⁶)
R¹⁷Represents R¹⁴~ R¹⁷Are an alkyl group, an aryl group,
Represents a heterocyclic group). n¹Represents 0 or 1. ] [2] In the general formula (1), Ch is an S atom.
The compound according to [1]. [3] In the general formula (1), Ch is an O atom.
The compound according to [1]. [4] In the general formula (2), n¹Is 0 [1]
~ The compound according to any one of [3]. [5] In the above general formula (1), R³, R⁶, R⁷, R
^TenIs a hydrogen atom and R^Four , R^Five, R⁸Are each a hydroxy group,
Alkoxy, aryloxy, or acyloxy
The compound according to any one of [1] to [4], which represents a group. However
R^Four, R^FiveAnd R ⁸Represents a hydroxy group at the same time
Absent. [6] In the general formula (1), R^Four, R⁶, R⁷, R
^TenIs a hydrogen atom and R³ , R^Five, R⁸Are each a hydroxy group,
Alkoxy, aryloxy, or acyloxy
The compound according to any one of [1] to [4], which represents a group. [7] In the above general formula (1), R³, R⁶, R⁸, R
^TenIs a hydrogen atom and R^Four , R^Five, R⁷Are each a hydroxy group,
Alkoxy, aryloxy, or acyloxy
The compound according to any one of [1] to [4], which represents a group. [8] In the above general formula (1), R³, R⁶, R⁷，
R⁹, R^TenIs a hydrogen atom and R ^Four, R^Five, R⁸Is each
Si group, alkoxy group, aryloxy group, acyloxy
The compound according to any one of [1] to [5], which represents a group. [9] For synthesizing the compound represented by the general formula (1)
To use a gold (I) compound represented by the following general formula (3)
A synthetic method characterized in that General formula (3) [L²-Au-L³] X_n2 [In Formula (3), L²And L³Both or less
One of them is N atom, S atom, Se atom, Te atom or
Compounds that can be coordinated to gold (I) via a P atom
(Excluding ruculphosphines and arylphosphines)
And the other represents a halogen atom. X is the charge of the compound
Is a counter salt required to neutralize²Is 0 or more and 1 or less
Represents a number and may be a decimal number. ]

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION The compound represented by formula (1) is described in detail below. The compound represented by the formula (1) is characterized in that it is a salt of gold (I) and an anionic sulfide such as glucose, mannose or galactose, in which the sulfur atom is substituted at the 1-position of the so-called sugar mother nucleus. The saccharide used in the present invention is, for example, glucose, mannose,
Galactose, gulose, xylose, lyxose, arabinose, ribose, fucose, idose, talose, allose, altrose, rhamnose, sorbose, digitoxose, 2-deoxyglucose, 2-
Deoxygalactose, fructose, glucosamine,
Galactosamine, glucuronic acid, etc. and their derivatives (here, derivatives are hydroxy group, amino group in sugar structure,
A carboxy group is an alkoxy group (including a group containing an ethyleneoxy group or a propyleneoxy group unit repeatedly),
Aryloxy group, acyloxy group, (alkyl, aryl, or heterocycle) amino group, acylamino group, sulfonamide group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, or the like, which is substituted), and sugars thereof 5-thiosaccharides in which the O atom in the 6-membered ring is replaced by an S atom. It is known that these saccharides have two types of structural isomers, D-form and L-form, which are enantiomers. However, in the range of use as medicines, agricultural chemicals and photographic materials, desired effects are obtained. It is expressed in both enantiomers. Preferred saccharide mother nuclei in the present invention are glucose, mannose, galactose, xylose,
Lyxose, arabinose, ribose, rhamnose, 2
-Deoxyglucose, 2-deoxygalactose, glucosamine, galactosamine and the like, more preferably glucose, mannose, galactose, xylose, lyxose, glucosamine, galactosamine and the like, more preferably glucose, mannose, galactose, xylose, glucosamine and the like. is there.

In the formula (1), Ch represents an O atom or an S atom. In the present invention, an O atom is preferable.

In the formula (1), one of R ¹ and R ² represents a group represented by the formula (2), and the other represents a hydrogen atom or an alkyl group. The alkyl group referred to here has 1 to 12 carbon atoms.
, A linear, branched or cyclic, substituted or unsubstituted alkyl group, preferably a linear, branched or cyclic, substituted or unsubstituted alkyl group having 1 to 7 carbon atoms, and more preferably It is a linear or branched, substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, and a hydroxymethyl group.

In the present invention, it is preferable that ^one of R ¹ and R ² represents a group represented by the formula (2) and the other represents a hydrogen atom.

In equation (2), L¹Is replaced or unplaced
An amine, a 5- to 6-membered nitrogen-containing heterocycle,
Alls (and their proton dissociation products), thioethers
, Disulfides, thioamides, selenoethers
, Diselenides, selenoamides, telluroethers
, Ditellurides, telluroamides, or P (R¹¹)
(R¹²) R ¹³(R¹¹~ R¹³Is a heterocyclic group, OR¹⁴, SR¹⁵, N (R¹⁶)
R¹⁷Represents R¹⁴~ R¹⁷Are an alkyl group, an aryl group,
Or represents a heterocyclic group). Also, L¹According to
When a charge is generated, the compound represented by formula (1) is a compound
Can have the necessary counter-salt to neutralize the charge of the product
It When the counter salt is an anion, it is specifically halogenium.
Ions (eg F^-, Cl^-, Br^-, I^-), Tetraful
Oroboronate ion (BF_Four ^-), Hexafluorophos
Honate ion (PF₆ ^-), Hexafluoroantimonet
Toion (SbF₆ ^-), Sulfate ion (SO_Four ^2-), A
Reel sulfonate ion (eg p-toluene sulfo)
Nate ion, naphthalene-2,5-disulfonate
ON, etc.), carboxy ion (eg acetate ion,
Lifluoroacetate, oxalate, benzoate, etc.
And others). When the counter salt is a cation,
Alkali metal ions (eg lithium cation,
Sodium cation, potassium cation, etc.)
Lithium metal ions (eg magnesium ion, calci)
(Ion, etc.), substituted or unsubstituted ammonium
Ions (eg ammonium, triethylammonium)
, Tetramethylammonium, etc.), substituted or not
Substituted pyridinium ions (eg pyridinium, 4-
Phenylpyridinium etc.) and the like. The present invention
In, it is preferable that the counter salt is a cation, and
Preferred are alkali metal ions and alkaline earth metal ions.
Or a substituted or unsubstituted ammonium ion.

In the formula (2), when L ¹ is a substituted or unsubstituted amine, ammonia, a primary, secondary, or tertiary alkylamine having 1 to 30 carbon atoms,
Or a substituted or unsubstituted 1 to 6 to 30 carbon atom
Examples include secondary, secondary, or tertiary anilines.
Specific examples thereof include benzylamine, ethylenediamine, butylamine, dibutylamine, triethylamine, aniline and dimethylaniline.

In the formula (2), when L ¹ is a 5- or 6-membered nitrogen-containing heterocycle, the heterocycle is a 5- or 6-membered nitrogen-containing heterocycle consisting of a combination of nitrogen, oxygen, sulfur and carbon. Is mentioned. The nitrogen-containing heterocycle may have a substituent. The substituent as used herein includes, for example, a halogen atom (fluorine atom, chlorine atom, bromine atom, or iodine atom), an alkyl group (a linear, branched, or cyclic alkyl group, including a bicycloalkyl group and an active methine group), Alkenyl group, alkynyl group, aryl group, heterocyclic group (regardless of substitution position), acyl group, alkoxycarbonyl group, aryloxycarbonyl group, heterocyclic oxycarbonyl group, carbamoyl group, N-hydroxycarbamoyl group, N- Acylcarbamoyl group, N
-Sulfonylcarbamoyl group, N-carbamoylcarbamoyl group, thiocarbamoyl group, N-sulfamoylcarbamoyl group, carbazoyl group, carboxy group or a salt thereof, oxalyl group, oxamoyl group, cyano group, carbonimidoyl group (Carbonimidoyl group), Formyl group,
A hydroxy group, an alkoxy group (including a group containing an ethyleneoxy group or a propyleneoxy group unit repeatedly),
Aryloxy group, heterocyclic oxy group, acyloxy group, (alkoxy or aryloxy) carbonyloxy group, carbamoyloxy group, sulfonyloxy group, amino group, (alkyl, aryl or heterocyclic) amino group, acylamino group, sulfonamide group , Ureido group, thioureido group, N-hydroxyureido group, imide group, (alkoxy or aryloxy)
Carbonylamino group, sulfamoylamino group, semicarbazide group, thiosemicarbazide group, hydrazino group, ammonio group, oxamoylamino group, N- (alkyl or aryl) sulfonylureido group, N-acylureido group, N-acylsulfamoyl group Amino group, hydroxyamino group, nitro group, heterocyclic group containing a quaternized nitrogen atom (eg, pyridinio group, imidazolio group, quinolinio group, isoquinolinio group), isocyano group, imino group, mercapto group, (alkyl, aryl Or a heterocycle) thio group, (alkyl, aryl, or heterocycle) dithio group, (alkyl or aryl) sulfonyl group, (alkyl or aryl) sulfinyl group,
Examples thereof include a sulfo group or a salt thereof, a sulfamoyl group, an N-acyl sulfamoyl group, an N-sulfonylsulfamoyl group or a salt thereof, and a silyl group. Here, the active methine group means a methine group substituted with two electron-withdrawing groups, and the electron-withdrawing group here means an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, Alkylsulfonyl group, arylsulfonyl group, sulfamoyl group, trifluoromethyl group, cyano group, nitro group, carbonimidoyl group (Carbonimidoyl group
Group) is meant. Here, the two electron-withdrawing groups may be bonded to each other to form a cyclic structure. The salt means a cation such as an alkali metal, an alkaline earth metal or a heavy metal, or an organic cation such as an ammonium ion or a phosphonium ion.

These substituents may be further substituted with these substituents.

The nitrogen-containing heterocyclic group represented by L ¹ is preferably a substituted or unsubstituted benzotriazole, triazole, tetrazole, indazole, benzimidazole, imidazole, benzothiazole, thiazole, thiazoline, benzoxazole, benzoxazoline, oxazole, Thiadiazole, oxadiazole, triazine, pyrrole, pyrrolidine, imidazolidine, morpholine, and the like, more preferably substituted or unsubstituted, benzotriazole, triazole, tetrazole, indazole, most preferably substituted or unsubstituted. Benzotriazole.

The thiol compound (and its proton dissociation product) represented by L ¹ in the formula (2) is specifically an alkyl thiol compound, an aryl thiol compound, a heterocyclic thiol compound and a respective proton dissociation compound. In addition, these thiol compounds (and their proton dissociation products) may be substituted, and typical examples of the substituents include the same as those described above.

In the formula (2), the alkyl group contained in the alkylthiol compound represented by L ¹ (and its proton dissociation product) is a substituted or unsubstituted, straight-chain, branched or cyclic group having 1 to 30 carbon atoms. And preferably an alkyl group having 1 to 20 carbon atoms.

In the formula (2), the aryl group contained in the aryl thiol compound represented by L ¹ (and its proton dissociation product) is a substituted or unsubstituted monocyclic or condensed ring aryl group having 6 to 30 carbon atoms. A group such as a phenyl group or a naphthyl group. It is preferably a substituted or unsubstituted phenyl group.

The heterocyclic group contained in the heterocyclic thiol compound (and its proton dissociation product) represented by L ¹ in the formula (2) is a 5- to 7-membered compound containing at least one of a nitrogen atom, an oxygen atom and a sulfur atom. A cyclic, substituted or unsubstituted, saturated or unsaturated heterocycle. These may be a single ring or may form a condensed ring together with other aryl ring or hetero ring. The heterocyclic group is preferably a 5- or 6-membered one, for example, a pyrrolyl group,
Pyrrolidinyl group, pyridyl group, piperidyl group, piperazinyl group, imidazolyl group, pyrazolyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, triazolyl group, tetrazolyl group, quinolyl group, isoquinolyl group, indolyl group, indazolyl group, benzimidazolyl group,
Pyranyl group, chromenyl group, thienyl group, oxazolyl group, oxadiazolyl group, thiazolyl group, thiadiazolyl group, benzoxazolyl group, benzothiazolyl group, morpholino group, morpholinyl group, etc., 1,4,5-trimethyl-1,2,2, Mesoionic compounds such as 4-triazolium-3-thiolate may be mentioned.

Preferred thiol compounds in the present invention are 2-aminoethanethiol, cysteine, thiophenol, 4-carboxythiophenol, 1,4,5-
Trimethyl-1,2,4-triazolium-3-thiolate, 1-thio-β-D-glucose, 1-thio-α-D
-Glucose, 1-thio-α-D-mannose, 1-thio-β-D-galactose, 1-thio-β-D-xylose, 2,3,4,6-tetraacetyl-1-thio-β- D-glucose, 2,3,4,6-tetraacetyl-1-thio-α-D-mannose and the like can be mentioned.

The thioether represented by L ¹ in the formula (2) is a thioether compound in which an alkyl group, an aryl group, or a heterocyclic group is bonded to a sulfur atom, and the sulfur atom may be symmetrically substituted or asymmetrically substituted. And specifically include dialkyl thioethers, diaryl thioethers, diheterocyclic thioethers, alkyl-aryl thioethers, alkyl-heterocyclic thioethers, aryl-heterocyclic thioethers, and the like. The alkyl group, aryl group and heterocyclic group of the thioether compound represented by L ¹ may be substituted, and typical substituents are the same as those described above.

In the formula (2), the alkyl group contained in the thioether compound represented by L ¹ has 1 to 30 carbon atoms,
A substituted or unsubstituted, straight-chain, branched or cyclic one, preferably an alkyl group having 1 to 20 carbon atoms.

In the formula (2), the aryl group contained in the thioether compound represented by L ¹ has 6 to 30 carbon atoms,
A substituted or unsubstituted monocyclic or condensed ring aryl group, for example, a phenyl group or a naphthyl group. It is preferably a substituted or unsubstituted phenyl group.

In the formula (2), the heterocyclic group of the thioether compound represented by L ¹ is a substituted or unsubstituted 5- to 7-membered ring containing at least one of nitrogen atom, oxygen atom and sulfur atom. , A saturated or unsaturated heterocycle. These may be a single ring or may form a condensed ring together with other aryl ring or hetero ring. The heterocyclic group is preferably a 5- or 6-membered one, for example, a pyrrolyl group, a pyrrolidinyl group, a pyridyl group,
Piperidyl group, piperazinyl group, imidazolyl group, pyrazolyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolyl group, isoquinolyl group, indolyl group, indazolyl group, benzimidazolyl group, pyranyl group, chromenyl group, thienyl group, oxazolyl group, thiazolyl group , Benzoxazolyl group, benzothiazolyl group, morpholino group, morpholinyl group and the like.

Preferred thioether compounds in the present invention are symmetrical or asymmetrical dialkyl thioethers, diaryl thioethers and alkyl-aryl thioethers, specifically thiodiethanol, 2
-Methylthioethanol, methionine, S-methylcysteine, 2-methylthioethanesulfonic acid, tetrahydrothiophene, dibenzylthioether, bis (4-carboxyphenyl) thioether, butylphenylthioether and the like can be mentioned.

The disulfide represented by L ¹ in the formula (2) is a disulfide compound in which an alkyl group, an aryl group or a heterocyclic group is bonded to a sulfur atom, and the disulfide group may be symmetrically substituted or asymmetrically substituted. And specifically include dialkyl disulfides, diaryl disulfides, diheterocyclic disulfides, alkyl-aryl disulfides, alkyl-heterocyclic disulfides, aryl-heterocyclic disulfides and the like. Preferred disulfides in the present invention are symmetrical or asymmetrical dialkyl disulfides, diaryl disulfides or alkyl-aryl disulfides. The alkyl group, aryl group and heterocyclic group of the disulfide compound represented by L ¹ may be substituted, and typical examples of the substituent include the same as those described above.

In formula (2), the alkyl groups of the disulfide compound represented by L ^1, an aryl group or a heterocyclic group has the same meaning as that L ¹ is a thioether compound, its preferred range is also the same . Specific examples include cystine, bis (4-carboxyphenyl) disulfide, diphenyl disulfide, dibutyl disulfide and the like.

In the formula (2), when L ¹ is a thioamide, the thioamide group may be a part of the ring structure or an acyclic thioamide group. Useful thioamides include, for example, US Pat. No. 4,030,925.
Issue 4,031,127, Issue 4,080,207
Nos. 4,245,037, 4,255,511
Nos. 4,266,031 and 4,276,36
No. 4 and Research Disclosure (Research D
isclosure) Volume 151, November 1976, 1516
2 and 176, December 1978, 1762.
It can be selected from those disclosed in Section 6. L ¹
Is a thioamide, preferred thioamide compounds are thiourea, thiourethane, dithiocarbamic acid ester,
4-thiazolin-2-thione, thiazolidine-2-thione, 4-oxazoline-2-thione, oxazolidine-
2-thione, 2-pyrazolin-5-thione, 4-imidazoline-2-thione, 2-thiohydantoin, rhodanine, isorhodanine, 2-thio-2,4-oxazolidinedione, thiobarbituric acid, tetrazoline-5-thione , 1,2,4-triazoline-3-thione, 1,
3,4-thiadiazoline-2-thione, 1,3,4-oxadiazoline-2-thione, benzimidazoline-2
-Thione, benzoxazoline-2-thione, benzothiazoline-2-thione and the like, which may be further substituted, and typical substituents include the same substituents as described above.

[0031] formula (2), if L ¹ is a seleno-ether compounds, as examples of L ¹ is the case where L ¹ is a thioether compound, a compound obtained by replacing a sulfur atom selenium atom and the like, the preferred range Is also the same.
Specifically, selenodiethanol, 2-methylselenoethanol, selenomethionine, Se-methylselenocysteine, 2-methylselenoethanesulfonic acid, dibenzylselenoether, bis (4-carboxyphenyl) selenoether, butylphenylselenoether, etc. Is mentioned.

[0032] In the formula (2), if L ¹ is a diselenide compound, as examples of L ¹ is the case where L ¹ is a disulfide compound, include compounds obtained by replacing a sulfur atom selenium atom, preferable range It is also the same. Specific examples include selenocistin, bis (4-carboxyphenyl) diselenide, diphenyl diselenide, dibutyl diselenide, and the like.

[0033] If it is L ¹ is selenoamides compound in formula (2), as examples of L ¹ is the case where L ¹ is a thioamide compound, include compounds obtained by replacing a sulfur atom selenium atom, but also the preferred ranges It is the same. Specifically, selenoureas, selenourethanes, diselenocarbamic acid esters, 4-thiazoline-2-theron, thiazolidine-2-theron, 4-oxazoline-2-theron, oxazolidine-2-theron, 2-pyrazolin-5- Theron, 4-imidazoline-2-theron, tetrazoline-5
-Theron, 1,2,4-triazoline-3-theron,
1,3,4-thiadiazoline-2-theron, 1,3,4
-Oxadiazoline-2-theron, benzimidazoline-2-theron, benzoxazoline-2-theron, benzothiazoline-2-theron and the like can be mentioned.

[0034] formula (2), if L ¹ is a Teruroeteru compound, as examples of L ¹ is the case where L ¹ is a thioether compound, a compound obtained by replacing a sulfur atom and tellurium atom. A preferred range Is also the same.
Specifically, tellurodiethanol, 2-methylteluroethanol, telluromethionine, Te-methyltellocysteine, 2-methyltelloethanesulfonic acid, dibenzyltelloether, bis (4-carboxyphenyl) telloether, butylphenyltelloether, etc. Is mentioned.

[0035] If the expression is L ¹ in (2) is a ditelluride compound, as examples of L ¹ is the case where L ¹ is a disulfide compound, include compounds obtained by replacing a sulfur atom tellurium atom, but also the preferred ranges It is the same. Specific examples thereof include tellurocystin, bis (4-carboxyphenyl) ditelluride, diphenyl ditelluride, dibutyl ditelluride, and the like.

[0036] Equation (2) When L ¹ is a Teruroamido compound in, as examples of L ¹ is the case where L ¹ is a thioamide compound, include compounds obtained by replacing a sulfur atom tellurium atom, but also the preferred ranges It is the same. Specifically, tellurourea, tellurourethane, diterrocarbamic acid ester, 4-thiazoline-2-terone, thiazolidine-2-terone, 4-oxazoline-2-terone, oxazolidine-2-terone, 2-pyrazoline-5- Teron, 4-imidazoline-2-terone, tetrazoline-5
-Terone, 1,2,4-triazoline-3-terone,
1,3,4-thiadiazoline-2-terone, 1,3,4
-Oxadiazoline-2-terone, benzimidazoline-2-terone, benzoxazoline-2-terone, benzothiazoline-2-terone and the like.

In the formula (2), when L ¹ is a compound capable of coordinating to gold (I) via a P atom, specifically, P 1
(R ¹¹ ) (R ¹² ) R ¹³ (R ^{11 to} R ¹³ are heterocyclic groups, OR ¹⁴ , SR ¹⁵ , N
Represents ^{(R 16) R 1 7,} R 14 ~R 17 is an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, be represented by a heterocyclic group having 5 to 12 carbon atoms) it can. R ^{11 to} R ¹³ are, for example, pyridyl group, imidazolyl group, quinolyl group, benzimidazolyl group, pyrimidyl group, pyrazolyl group, isoquinolinyl group, thiazolyl group, thienyl group, furyl group, benzothiazolyl group, methoxy group, ethoxy group, butoxy group, Isopropoxy group, phenoxy group, methylthio group,
Examples thereof include a butylthio group, a phenylthio group, a dimethylamino group, a diethylamino group and a diphenylamino group.

In the present invention, L ¹ is preferably a 5- to 6-membered nitrogen-containing heterocycle, thiols (and their proton dissociation products), thioethers, thioamides, and selenoamides, and more preferably 5 to 6 Membered nitrogen-containing heterocycles, thiols, thioethers and thioamides, most preferably thiols, thioethers and thioamides.

Specific examples of L ^{1 which} can be used in the present invention are shown below, but the present invention is not limited thereto.

[0040]

[Chemical 5]

[0041]

[Chemical 6]

[0042]

[Chemical 7]

In the formula (2), n ¹ represents 0 or 1. In the present invention, n ¹ is preferably 0.

In the formula (1), R ^{3 to} R ¹⁰ are each a hydrogen atom, an alkyl group, a hydroxy group, an amino group, a carboxy group, an alkoxy group, an aryloxy group, an acyloxy group, an acylamino group, a sulfonamide group, an alkoxycarbonyl group. Represents a group, an aryloxycarbonyl group, or a carbamoyl group. The alkyl group referred to here is R ¹ or
The same applies to the description for R ² and the preferred range is also the same. The amino group represented by R ^{3 to} R ¹⁰ is preferably an amino group having 0 to 12 carbon atoms, more preferably 0 to 6, and examples thereof include an amino group, a methylamino group and a dimethylamino group. To be The alkoxy group represented by R ^{3 to} R ¹⁰ is preferably an alkoxy group having 1 to 12 carbon atoms, more preferably 1 to 7 carbon atoms, for example, methyloxy group, ethyloxy group, butyloxy group, benzyl. An oxy group etc. are mentioned. The aryloxy group represented by R ^{3 to} R ¹⁰ is preferably an aryloxy group having 6 to 12 carbon atoms, more preferably 6 to 12 carbon atoms, and examples thereof include a phenyloxy group. The acyloxy group represented by R ^{3 to} R ¹⁰ preferably has 2 to 1 carbon atoms.
2 acyloxy groups, more preferably 2 to 2 carbon atoms.
8 and examples thereof include an acetyloxy group, a propanoyloxy group, a butyroyloxy group, a pivaloyloxy group, a benzoyloxy group and a p-methoxyphenylcarbonyloxy group. The acylamino group represented by R ^{3 to} R ¹⁰ is preferably an acylamino group having 2 to 12 carbon atoms, more preferably 2 to 8 carbon atoms, for example, acetylamino group, propanoylamino group, butyroyl. Examples thereof include an amino group, a pivaloylamino group and a benzoylamino group. The sulfonamide group represented by R ^{3 to} R ¹⁰ is preferably a sulfonamide group having 2 to 12 carbon atoms, more preferably 1 to 8 carbon atoms, and examples thereof include a methanesulfonamide group and an ethanesulfonamide group. , Trifluoromethanesulfonamide group, benzenesulfonamide group, p-toluenesulfonamide group and the like.
The alkoxycarbonyl group represented by R ^{3 to} R ¹⁰ is preferably an alkoxycarbonyl group having 2 to 12 carbon atoms, more preferably 2 to 8 carbon atoms, and examples thereof include a methoxycarbonyl group, an ethoxycarbonyl group, and a butyrene group. Roxycarbonyl group, benzyloxycarbonyl group and the like can be mentioned. The aryloxycarbonyl group represented by R ^{3 to} R ¹⁰ is preferably an aryloxycarbonyl group having 7 to 18 carbon atoms, more preferably 7 to 12 carbon atoms,
Examples thereof include a phenoxycarbonyl group. R ³ ~
The carbamoyl group represented by R ¹⁰ is preferably a carbamoyl group having 1 to 12 carbon atoms, more preferably 1 to 8 carbon atoms, and examples thereof include a carbamoyl group, an N-methylcarbamoyl group and an N-butylcarbamoyl group. , N-phenylcarbamoyl group and the like. In the present invention, R ^{3 to} R
Each of ¹⁰ is preferably a hydrogen atom, an alkyl group, a hydroxy group, an amino group, an alkoxy group, an acyloxy group, or an acylamino group, and more preferably a hydrogen atom, an alkyl group, a hydroxy group, an alkoxy group, or an acyloxy group.

In the present invention, the compound represented by the formula (1)
Of these, the preferred one is R¹And R²One of the general formulas
N in (2)¹Is a group representing 0 and the other is a hydrogen atom or
Is an alkyl group, R³And R^FourOne of them is a hydrogen atom
The other is hydrogen atom, alkyl group, hydroxy group, amino
Group, alkoxy group, aryloxy group, acyloxy
A group or an acylamino group, R^FiveAnd R⁶One side
Is a hydrogen atom and the other is a hydrogen atom, alkyl group, hydroxy
Group, amino group, alkoxy group, aryloxy group, acyl group
Roxy group or acylamino group, R⁷and
R⁸One is a hydrogen atom and the other is a hydrogen atom, an alkyl group,
Hydroxy group, amino group, alkoxy group, aryloxy
A Si group, an acyloxy group, or an acylamino group,
R⁹And R^TenOne is a hydrogen atom and the other is a hydrogen atom,
Alkyl group, hydroxy group, amino group, carboxy group,
Lucoxy group, aryloxy group, acyloxy group,
Is the case of an acylamino group. More preferably R¹
And R²One is n in the general formula (2).¹Represents 0
The other of the groups is a hydrogen atom, R³And R^FourOne side is hydrogen
The other is hydrogen atom, hydroxy group, amino group,
Coxy group, aryloxy group, acyloxy group, or
An acylamino group, R^FiveAnd R⁶One of is a hydrogen atom
And the other is hydrogen atom, hydroxy group, alkoxy group,
Is an alkyloxy group or an acyloxy group, and R⁷And
And R⁸One is a hydrogen atom and the other is a hydrogen atom, hydroxy
Group, alkoxy group, aryloxy group, or acyl group
A xy group, R⁹And R^TenOne is a hydrogen atom and the other is
Is a hydrogen atom, alkyl group, or carboxy group
It is the case. More preferably R¹And R²One of the general formulas
N in (2)¹Is a group representing 0 and the other is a hydrogen atom
R³And R^FourOne is a hydrogen atom and the other is a hydrogen atom,
Hydroxy group, amino group, alkoxy group, aryloxy
A Si group, an acyloxy group, or an acylamino group,
R^FiveAnd R⁶One is a hydrogen atom and the other is a hydroxy group,
Alkoxy, aryloxy, or acyloxy
Group, R⁷And R⁸One is a hydrogen atom and the other is a hydr
Roxy group, alkoxy group, aryloxy group, or
A siloxy group, R⁹And R^TenOne of is a hydrogen atom
And when the other is a hydrogen atom or an alkyl group,
It Most preferably R¹And R²One of the general formula (2)
At n¹R is a group in which the other is a hydrogen atom,³
Is a hydrogen atom and R^FourIs an amino group, alkoxy group, aryl
An oxy group, an acyloxy group, or an acylamino group
R^FiveIs an alkoxy group, an aryloxy group, or
R at the siloxy group⁶Is a hydrogen atom, and R⁷Is a hydrogen atom
R⁸Is an alkoxy group, aryloxy group, or acyl
An oxy group, R⁹R is an alkyl group^TenIs a hydrogen atom
If yes, or R¹And R²One of the general formula (2)
At n¹R is a group in which the other is a hydrogen atom,³But
Hydroxy group, alkoxy group, aryloxy group,
R is an acyloxy group^FourIs a hydrogen atom, and R^FiveIs hydro
An oxy group, an alkoxy group, an aryloxy group, or an acyl group.
R is R ⁶Is a hydrogen atom, and R⁷Is a hydrogen atom and R
⁸Is a hydroxy group, an alkoxy group, an aryloxy group,
Or an acyloxy group, R⁹Is a hydrogen atom, or
R is an alkyl group^TenIs a hydrogen atom, or R¹Oh
And R²One is n in the general formula (2).¹Is a group in which 0 represents
And the other is a hydrogen atom, R³Is a hydrogen atom and R^FourIs hydro
Xy group, amino group, alkoxy group, aryloxy group,
An acyloxy group or an acylamino group, R^FiveBut
Hydroxy group, alkoxy group, aryloxy group,
R is an acyloxy group⁶Is a hydrogen atom, and R⁷Is hydro
An oxy group, an alkoxy group, an aryloxy group, or an acyl group.
R is R⁸Is a hydrogen atom, and R⁹Is a hydrogen atom
Or alkyl group R^TenIs a hydrogen atom, or
R¹And R²One is n in the general formula (2).¹Represents 0
The other is a hydrogen atom, and R is³Is a hydrogen atom and R^FourBut hi
Droxy group, amino group, alkoxy group, acyloxy
A group or an acylamino group, R^FiveIs hydroxy
Group, alkoxy group, aryloxy group, or acyl group
R in xy group⁶Is a hydrogen atom, and R⁷Is a hydrogen atom and R⁸But
Hydroxy group, alkoxy group, aryloxy group,
Is an acyloxy group, R ⁹And R^TenIs a hydrogen atom
In some cases.

In the present invention, the general formula (1) is represented by JP-B-45.
-29274 mercaptoglucoside gold (I) salt (that is, in formula (1), one of R ¹ and R ² is a group in which n ¹ represents 0 in formula (2) and the other is a hydrogen atom, R ³ is a hydrogen atom, R ⁴ is a hydroxy group, and R ⁵
Is a hydroxy group, R ⁶ is a hydrogen atom, R ⁷ is a hydrogen atom, R ⁸ is a hydroxy group, R ⁹ is a hydroxymethyl group, and R ¹⁰ is a hydrogen atom). It is known that the 1-position of the saccharide is called the anomeric position and that there are α-type and β-type isomers as its three-dimensional structure. In the case of the mercaptoglucoside gold (I) salt, β can be selectively synthesized. In many cases, it is inconvenient from a practical point of view because the type gold salt is insoluble in water, and it is difficult to selectively produce a soluble α-type gold salt, and the β-type isomer must be mixed. This is because it is not preferred in the present invention because it is extremely difficult to produce while controlling the isomer ratio of the mixture of α-form and β-form to be constant.

Specific examples of the compound represented by the general formula (1) are shown below, but the invention is not limited thereto.

[0048]

[Chemical 8]

[0049]

[Chemical 9]

[0050]

[Chemical 10]

In the chemical formula, Ac represents an acetyl group, Bz represents a benzoyl group, and Bn represents a benzyl group. The compound of the present invention can be synthesized by using the gold (I) compound represented by the general formula (3). The compound represented by formula (3) is described in detail below. In equation (3),
Both or at least one of L ² and L ³ is a substituted or unsubstituted amine, 5- or 6-membered nitrogen-containing heterocycle, thioether, disulfide, thioamide,
Selenoethers, diselenides, selenoamides, telluroethers, ditellurides, telluroamides, or P (R ¹¹ ) (R ¹² ) R ¹³ (R ^{11 to} R ¹³ are heterocyclic groups, OR ¹⁴ , S
R ¹⁵ and N (R ¹⁶ ) R ¹⁷ are represented, and R ^{14 to} R ¹⁷ each represent an alkyl group, an aryl group, or a heterocyclic group), and the other represents a halogen atom. X is a counter salt necessary for neutralizing the charge of the compound, and n represents a number of 0 or more and 1 or less, and may be a decimal number. The compounds represented by L ² and L ³ have the same meanings as L ¹ in formula (1), respectively, and their preferred ranges are also the same. In the present invention, L ² and L ³ do not represent alkylphosphines and arylphosphines. Because these compounds are coordinated Au (I) compounds (for example, J. Med. Chem. 1972, 15, 1095
Chloro (triethylphosphine) gold (I) whose synthetic method is described on the page or Inorg. Synth. 1982, 21, 71 (triphenylphosphine) gold (I) etc. are used. However, since the complex formation stability constant between these phosphine compounds and gold (I) is strong, these phosphine compounds remain in the final isolated product, which is not preferable as the compound synthesis method of the present invention. Because.

In the formula (3), when L ² or L ³ is a halogen atom, it specifically represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, but in the present invention, the chlorine atom or the bromine atom is A chlorine atom is preferable and a chlorine atom is more preferable. In the present invention, it is preferable that L ² or L ³ represents a halogen atom.

In the formula (3), X represents a counter salt necessary for neutralizing the charge of the compound. When the counter salt represented by X is an anion, it is specifically a halogenium ion (for example, F ⁻ , Cl ⁻ , Br ⁻ , I ⁻ ), a tetrafluoroboronate ion (BF ₄ ⁻ ), a hexafluorophosphonate ion. (PF ₆ ^-), hexafluoroantimonate ion (S
bF ₆ ⁻ ), sulfate ion (SO ₄ ²⁻ ), arylsulfonate ion (for example, p-toluenesulfonate ion,
Naphthalene-2,5-disulfonate ion), carboxy ion (eg, acetate ion, trifluoroacetate ion, oxalate ion, benzoate ion, etc.) and the like. When the counter salt represented by X is a cation, specifically, an alkali metal ion (eg, lithium cation, sodium cation, potassium cation, etc.), an alkaline earth metal ion (eg, magnesium ion, calcium ion, etc.), substitution or Unsubstituted ammonium ion (eg ammonium, triethylammonium,
Tetramethylammonium, etc.) and substituted or unsubstituted pyridinium ions (eg pyridinium, 4-phenylpyridinium, etc.) and the like. In the present invention, the counter salt represented by X is preferably an anion, and more preferably a halogenium ion, a tetrafluoroboronate ion, a hexafluorophosphonate ion, a hexafluoroantimonate ion, a sulfate ion or an arylsulfonate ion. More preferably, it is a halogenium ion, a tetrafluoroboronate ion, a hexafluorophosphonate ion, or a hexafluoroantimonate ion.

Although n ² represents a number of 0 or more and 1 or less, 0 is preferable in the present invention.

Specific examples of the compound represented by the general formula (3) are shown below, but the invention is not limited thereto.

[0056]

[Chemical 11]

[0057]

[Chemical 12]

[0058]

The present invention will be described in detail below with reference to examples, but the present invention is not limited thereto. Exemplified Compound 2 was synthesized according to Scheme 1. Scheme 1

[0059]

[Chemical 13]

(Synthesis of Synthetic Intermediate 1) Pentaacetyl-
To a solution of 13 g of α-D-mannose in 60 ml of methylene chloride, 25 g of acetic acid solution with 30% hydrogen bromide was added. After stirring overnight at room temperature, 100 ml of ice water and 100 ml of methylene chloride are used.
The liquid was separated by adding ml. The organic layer is 30 ml of saturated aqueous sodium hydrogen carbonate solution and 30 ml of saturated aqueous sodium chloride solution.
After washing with, dried over sodium sulfate, and concentrated under reduced pressure. 60 ml of ethanol was added to the obtained oily substance, and the precipitated crystals were collected by filtration to obtain 11 g of Synthetic intermediate 1. (Synthesis of Synthetic Intermediate 2) 10.5 g of Synthetic Intermediate 1 and 1.9 g of thiourea were added to 100 ml of acetone, and the mixture was heated under reflux for 1 hour. The reaction solution was ice-cooled, and the precipitated crystals were collected by filtration to obtain 8 g of Synthetic intermediate 2. (Synthesis of Synthetic Intermediate 3) 6 g of Synthetic Intermediate 2 and 3.4 g of potassium t-butoxide were added to 100 ml of methanol, and the mixture was stirred at room temperature for 1 hour. The precipitated crystals were collected by filtration to obtain 1.5 g of Synthetic intermediate 3. (Synthesis of Exemplified Compound 1-2) Synthesis Intermediate 3 in 8 ml of water
Dissolve 2 g and chill with ice cooling 3 g of chloroauric acid in 10 ml of water
And an aqueous solution of Exemplified Compound 2-1 prepared by mixing 2.7 g of thiodiethanol were added dropwise. After stirring for 30 minutes, the precipitated crystals were collected by filtration to obtain 3 g of Exemplified compound 1-2. Elemental analysis value calculated as C ₆ H ₁₁ O ₅ SAu = 392.17 C 18.47, H 2.33, S 8.2
2, Au 50.48 (%) measured value C 18.36, H 2.45, S 8.1
4, Au 50.22 (%)

(Synthesis of Exemplified Compound 1-3) 2,3,4,6-pentaacetyl-α-D obtained by using potassium disulfite in place of sodium methoxide in the synthesis of Synthesis Intermediate 3 above. -Thiomannose potassium salt is reacted with an aqueous solution of Exemplified Compound 2-1 prepared in the same manner as above, and the resulting precipitate is collected by filtration to Exemplified Compound 1-3.
Got Elemental analysis value C ₁₄ H ₁₉ O ₉ SAu = 560.33, calculated value C 30.01, H 3.42, S 5.7
2, Au 35.15 (%) measured value C 29.91, H 3.52, S 5.5
1, Au 35.11 (%)

(Synthesis of Exemplified Compound 1-6) In the synthesis of Exemplified Compound 1-2 described above, 1,2,3,4,6-pentaacetyl-α-D-mannose is replaced by 1,2,3.
Exemplified compound 1-6 was obtained by performing substantially the same operation except that 4,6-pentaacetyl-β-D-galactose was used. Elemental analysis value C ₆ H ₉ O ₅ SAu = 390.17, calculated value C 18.47, H 2.33, S 8.2
2, Au 50.48 (%) measured value C 18.29, H 2.48, S 8.1
2, Au 50.27 (%)

(Synthesis of Exemplified Compound 1-9) In the synthesis of Exemplified Compound 1-2, 1,2,3,4,6-pentaacetyl-α-D-mannose is used in place of 1,2,3,3.
Exemplified compound 1-9 was obtained by performing substantially the same operation except that 4-tetraacetyl-β-D-xylose was used.
Got Elemental analysis _{C 6 H 9 O 5 SAu =} 362.16 Calculated C 16.58, H 2.50, S 8.8
5, Au 54.39 (%) measured value C 16.39, H 2.64, S 8.7
7, Au 54.21 (%)

(Synthesis of Exemplified Compound 1-17) In the synthesis of Exemplified Compound 1-2, 1,2,3,4,6-pentaacetyl-α-D-mannose is replaced by 1,2,2.
Exemplified compound 1-17 was obtained by performing substantially the same operation except that 3,4-tetraacetyl-β-D-arabinose was used. Elemental analysis _{C 6 H 9 O 5 SAu =} 362.16 Calculated C 16.58, H 2.50, S 8.8
5, Au 54.39 (%) measured value C 16.42, H 2.65, S 8.6
9, Au 54.18 (%)

(Synthesis of Exemplified Compound 1-21) In the synthesis of Exemplified Compound 1-2, 1,2,3,4,6-pentaacetyl-α-D-mannose is replaced by 1,2,2.
Exemplified Compound 1 was obtained by performing substantially the same operation except that 3,4-tetraacetyl-β-D-lyxose was used.
-21 was obtained. Elemental analysis _{C 6 H 9 O 5 SAu =} 362.16 Calculated C 16.58, H 2.50, S 8.8
5, Au 54.39 (%) measured value C 16.38, H 2.72, S 8.6
2, Au 54.14 (%)

(Synthesis of Exemplified Compound 1-43) Half of Exemplified Compound 2-1 used in the synthesis of Exemplified Compound 1-2 (that is, 5 ml of water is mixed with 1.5 g of chloroauric acid and 1.35 g of thiodiethanol). Exemplified compound 1-43 was obtained by substantially the same procedure except that the preparation was carried out). Elemental analysis value calculated as C ₁₂ H ₂₂ O ₁₀ S ₂ AuK = 626.50 C 23.01, H 3.54, S 10.2
4, Au 31.44 (%) measured value C 22.89, H 3.83, S 10.5
5, Au 31.10 (%)

(Synthesis of Exemplified Compound 1-46) 200 mg of Exemplified Compound 1-2 was dissolved in 10 mL of water, and 132 mg of thioglucose Na salt (purity 84%) was added to 4 mL of water.
The solution dissolved in was added. Add 100 parts of ethanol to this solution.
Exemplified compound 1-46 was obtained by collecting a precipitate that was precipitated by adding mL. Elemental analysis value C ₁₂ H ₂₂ O ₁₀ S ₂ AuNa = 610.39
Calculated as C 23.61, H 3.63, S 10.5
1, Au 32.27 (%) measured value C 23.49, H 3.81, S 10.4
4, Au 32.28 (%)

[0068]

Industrial Applicability According to the present invention, a gold-sulfur compound useful as a synthetic intermediate for pharmaceuticals, agricultural chemicals and photographic materials can be provided. Further, the sensitivity could be improved by adding it to the silver halide photographic light-sensitive material.

Claims (8)

[Claims] 1. The following general formula (1) or its enantiomer
A gold (I) -sulfur compound represented by: General formula (1) [Chemical 1] [In Formula (1), Ch represents an O atom or an S atom. R
¹And R²One represents a group represented by the general formula (2),
The other represents a hydrogen atom or an alkyl group. R³~ R^{1 0}Is each
Hydrogen atom, alkyl group, hydroxy group, amino group,
Ruboxy group, alkoxy group, aryloxy group, acyl
Oxy group, acylamino group, sulfonamide group, alcohol
Xycarbonyl group, aryloxycarbonyl group,
Represents a carbamoyl group, and is a compound represented by the formula (1)
Does not contain thioglucose gold (I) salt. ] General formula (2) [Chemical 2] [In formula (2), L¹Is a substituted or unsubstituted
And 5- or 6-membered nitrogen-containing heterocycles and thiols
(And its proton dissociator), thioethers, diss
Rufides, thioamides, selenoethers, disere
Nides, selenoamides, telluroethers, ditteruri
Or telluroamides, or P (R¹¹) (R¹²) R ¹³(R¹¹~ R
¹³Is a heterocyclic group, OR¹⁴, SR¹⁵, Or N (R¹⁶) R¹⁷To
Represent, R¹⁴~ R^{1 7}Are each an alkyl group, an aryl group, or
Represents a heterocyclic group). n¹Represents 0 or 1. ] 2. In the general formula (1) according to claim 1,
The compound according to claim 1, wherein Ch is an O atom. 3. In the general formula (2) according to claim 1,
The compound according to claim 1, wherein n ¹ is 0. 4. In the general formula (1) according to claim 1,
R ^3, R at ^6, R ^7, R ^{1 0} is hydrogen ^{atom, R 4, R 5, R} 8 is hydroxy group, an alkoxy group, an aryloxy group, claim 1, characterized in that an acyloxy group The compound according to any one of 1. However, R ⁴ , R ⁵ and R ⁸ do not simultaneously represent a hydroxy group. 5. In the general formula (1) according to claim 1,
R ^4, R at ^6, R ^7, R ^{1 0} is hydrogen ^{atom, R 3, R 5, R} 8 is hydroxy group, an alkoxy group, an aryloxy group, claim 1, characterized in that an acyloxy group The compound according to any one of 1. 6. In the general formula (1) according to claim 1,
R ^3, in ^{R 6, R 8, R 1} 0 is hydrogen ^{atom, R 4, R 5, R} 7 are each hydroxy group, an alkoxy group, claims, characterized in that an aryloxy group or an acyloxy group, 1 ~
4. The compound according to any one of 3 above. 7. In the general formula (1), R ³ , R ⁶ and R
In ^7, R ^9, R ¹⁰ is a hydrogen ^{atom, R 4, R 5, R} 8 are each a hydroxyl group, an alkoxy group, any one of the preceding claims, characterized in that an aryloxy group or an acyloxy group, The compound according to. 8. A gold (I) compound represented by the following general formula (3) is used for synthesizing the compound represented by the general formula (1) according to claim 1. I) -Synthesis of sulfur compounds. General formula (3) [L ² -Au-L ³ ] X _n2 [In the formula (3), both or at least one of L ² and L ³ is a substituted or unsubstituted amine, a 5- to 6-membered nitrogen-containing compound. Heterocycles, thioethers, disulfides, thioamides, selenoethers, diselenides, selenoamides, telluroethers, ditellurides, telluroamides, or P (R ¹¹ ) (R ¹² ) R ¹³ (R ^{11 to} R ¹³
Represents a heterocyclic group, OR ¹⁴ , SR ¹⁵ , N (R ¹⁶ ) R ¹⁷ , and R ^{14 to} R
¹⁷ represents an alkyl group, an aryl group, or a heterocyclic group), and the other represents a halogen atom. X is a counter salt necessary for neutralizing the charge of the compound, and n ² represents a number of 0 or more and 1 or less, and may be a decimal number. ]